Hydrochloric Acid → 4'-Pentyloxybiphenyl-4-boronic Acid

HRID 1736290

Reaktionsgleichung

Reaktionsgleichung von HRID 1736290
[CH2:1]([O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16](Br)=[CH:15][CH:14]=2)=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH3:5].C([Li])CCC.C([O:28][B:29](OC(C)C)[O:30]C(C)C)(C)C.Cl>O1CCCC1>[CH2:1]([O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([B:29]([OH:30])[OH:28])=[CH:15][CH:14]=2)=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 28013884-Bromo-4'-(pentyloxy)-1,1'-biphenylHCID 178418339Butyllithium

Produkt 1

HCID 113580714'-Pentyloxybiphenyl-4-boronic AcidAusbeute 84,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a stirred suspension of 4-(4-n-pentoxyphenyl)bromobenzene (1.0 g, 3.13 mmol) in anhydrous tetrahydrofuran (20 mL) at -78° C. under a nitrogen atmosphere was added n-butyllithium in hexanes (2.5M, 1.32 mL, 3.30 mmol). After a period of 15 min, triisopropylborate (760 mL, 3.30 mmol) was added. Stirring at -78° C. was continued for 15 min and then at 25° C. for 40 min. The mixture was acidified with 0.5N HCl (20 mL) and then partitioned between ether (50 mL) and water (40 mL). The organic phase was washed with water (3×) and brine and dried with magnesium sulfate. The solvent was removed in vacuo to give 4-(4-n-pentoxyphenyl)phenylboronic acid (750 mg) as a white solid.

Aufarbeitung

  1. waitwas continued for 15 min
  2. waitat 25° C. for 40 min
  3. custompartitioned between ether (50 mL) and water (40 mL)
  4. washThe organic phase was washed with water (3×) and brine
  5. dry with materialdried with magnesium sulfate
  6. customThe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-bcdd181103bc484980085542ed117188
Quelldatensatz
uspto-grants-1996_07
Patentnummer
US05541160

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